March 6, 2014

10 Reasons Why You Should Try Cross-dressing. (Hint: it’s about self-growth). ~ Blake Stone


What if there are as many genders as there are people?

Disregard pronouns for the moment; at base pronouns are signifiers that may have very little to do with who or what they actually suggest.

Cross-dressing myths:

First off, cross-dressing doesn’t need to be about becoming the “other” gender. Cross-dressing also does not necessarily have anything to do with sexual arousal or even any interpersonal interactions. It’s about you and how your body feels when you do certain activities or dress in certain clothes, which you consider to be not of your gender.

For instance, I was born a female, but I identify as both a woman and a gender-queer (or neutral). Cross-dressing for me is actually dressing as a woman, wearing makeup, a dress and etc.

No need for full drag!

For some people a little mirror time with a feminine looking scarf, earrings, or drawing on a mustache is just enough.

One more thing: Cross-dressing does not have to go much farther than your own vanity. Sometimes I get caught up in negative thoughts about how vain it is to spend time in front of the mirror, but then I remember almost every woman I know spends more time in front of the mirror on a daily basis than I do in a week.

To paraphrase Jane Austen: “Vanity is a focus on what others think of us.”

Therefore, it matters not whether you are shaving or covering your face with make-up, you’re probably already considered vain.

So here are the 10 reasons I think you should give cross-dressing a try:

1. If you have never cross-dressed before it can offer you many insights about yourself and others. Unless you are very balanced, cross-dressing offers a glimpse into another part of yourself you may not have visually connected with before. You may see resemblances to family members you’ve never noticed or feel more vulnerable than you have in years. You may suddenly have memories of events from childhood pop up you haven’t thought of in forever. You will never know until you try.

2. Doing activities of the “other” gender may not only help you relate more with others, but it also gives you new knowledge about the world in general. If you hang around with people engaged in activities generally thought of as “women/men’s work,” like in a knitting group or doing construction projects, you may not only learn to knit or use tools, but you could expand your capacity to exist and learn in realms that many don’t even bother with.

3. Need to learn to laugh at or with yourself? I don’t know of any rules stating cross-dressing must be serious. In fact, if you’re doing it right, as a rule you should be laughing your ass off. Sure, there are some somber moments of maybe missing your dead grandmother who you now look like, but there’s also the fact that you look Fabulous! And maybe even downright ridiculous!

Last I checked there’s nothing wrong with either of these, but do check yourself: imitating gender stereotypes because you think it’s funny may be offensive to others. Keep in mind people take this shit seriously. Yo. Cross-dressing doesn’t actually make you the “other” gender, which leads to…

4. Regardless of your gender: Masculinity is doing, Femininity is being. How can you do anything without being? How can you be without doing? Shiva and Kali, yin and yang, etc. these are energetic houses where no one lives. None of us are totally in either, we must be, to do; and do, to be.

This may be why the duality of it all is an illusion. When you cross-dress, you are attempting to inhabit one of these houses (or maybe another house entirely), which is ultimately: unsustainable. This is why you are cross-dressing, not transitioning to another gender. Cross-dressing forces one to acknowledge that what they see in the “other/s” gender is within them, and what one may lay claim to in their own gender flourishes within the “other/s” as well.

5. Your parents will love you more. No, I’m not kidding. If you’re lucky enough to still have parents and even luckier enough to be close to them, cross-dressing can help deepen your relationship with each of them.

Chances are, your parents are heterosexuals, who to some extent buy into hetero-normative gender roles, which can be restrictive and limiting to personal growth. Now you know why your father spends so much time staring off into space, or why your mother acts a certain way; you see it in yourself now. Of course, they need not know the source of your new understandings, just that you have newfound compassion and appreciation of their existence.

6. Fire. Sex. Don’t get too excited (or do) but cross-dressing can involve sex. Yes cross-dressing will help your sex life but this is assuming your partner is a little experimental. How? There are so many things you can do!

Maybe your partner thinks you’re hot with a wig or boxer briefs on, maybe not. Regardless of whether you have a partner, you can still penetrate yourself and journal about it. If you’ve never been really penetrated, it can be a tremendous learning opportunity.

Did you know vaginal penetration could be horribly painful? Personally, I cried the first three times from the pain, and then the first ten times out of disbelief and shock that women actually let people do this to their bodies (later I used a hairbrush handle to build up my PVC muscles and went on my merry way).

If you’re curious about what it’s like to be penetrated, don’t avoid experimenting just because it sounds painful. Penetration is another realm of experience that you can benefit from; there’s no rule you must confine yourself to only a giver or only a receiver, we can all be both.

Do read up on the do’s and don’t of anal sex before you try, but also know anal sex is for everyone! The good news is we all have anuses so it can pleasurable for anyone (barring some victims of sexual assault). Please remember consent and gentleness is key.

You can also wear a strap on and jump up and down! Try wearing boxer briefs on top of your strap-on because your purple cock is like totally normal anatomy, yo. By experimenting with cross-dressing and sex, even if you’re in a hetero relationship, you can still have queer sex (tip: it’s pleasurable and leads to less babies).

7. This brings me to dildos. No matter who you are, if you’re serious about cross-dressing, dildos are amazing. Dildos! Whether you rock it with your cock out, or you want to experiment with your body, dildos offer a great way to connect with the different realms of experience. You can actually strap a dildo to any thing or body part.

There’s really no reason to put one on your crotch for sex when you can have one somewhere a lot less awkward. There are dildos for “packing,” which is fun if someone who likes semi-flaccid cock is into you or if a sock just doesn’t do it for you. There are also now 100% silicon hyper-realistic dildos that are great for gender play.

Personally, I’m not all that into gender play in sex, but I realize it is exciting new territory for many people. What is having a cock like? You may be surprised by what you can feel and the copulating instincts that magically arise. What is it like to fill yourself and be both the giver and receiver? Remember dildos are “eternally hard,” so you can meditate and rock yourself into orgasmic oblivion for hours if you want to.

[Skeptical? Why would we want to covet fake pieces of flesh in the name of physical pleasure or curiosity? Why objectify and abstract male anatomy into material objects that ultimately uses Mother Earth’s resources to create and destroy when we have real ones to enjoy naturally? Here’s the succinct argument: Being able to pleasure one’s self without the help of another person works towards autonomy and fulfillment of that individual regardless of sex or gender. Autonomy is a type of independence that is necessary for a life worth living. While females have clitorises, they also have multiple g-spots, which cannot be reached digitally. Males have prostates, which also may not be reached digitally; therefore, we must have tools to help us. This is not a novel idea, nor is the phallus a proprietary shape. Dependence on another for sexual pleasure does not work towards individual autonomy, but against it. The skinny: dildos are part of complete breakfast.]

8. Still reading? Congratulations, you have a healthy attention span. Cross-dressing can help you nurture this attention span. How? It endeavors you to pay attention. How do you know what cross-dressing is for you unless you are mindful of your bodily sensations, emotions and the wicked awesome heels you would not have seen had you not developed a keen eye. Seriously though, cross-dressing can lead to more body awareness, which is linked with focus and mindfulness.

9. Yoga: as I said above in number four, masculine is doing, feminine is being. None of us are totally in either, we must be, to do; and do, to be. While the notion of the pure masculine/feminine may be an illusion, many of us act as if they are attainable.

This leads to imbalances because it produces the effect of repression. Yes, girlie girls and butch men exist but not really. The accessories of the girlie girls and butch men are merely pop cultural fodder and fall away as the individuals grow older and further away from the “ideal” of what their gender is, which is usually dependent on things like youthfulness and physical strength.

Cross-dressing can help balance things out a bit and prepare one for what is to come. The clothes we wear are not biologically determined; there is no natural reason for anyone to wear a dress or anything else other than for aesthetic and social reasons.

The way you define your femininity may not be the way I define it for myself and likewise with masculinity. There’s really no greater way to find out exactly how you are defining and hiding these concepts from yourself and others than cross-dressing.

As I said before, cross-dressing doesn’t have to be a drag (pun), and it doesn’t have to be clothing: it can be an activity. The yoga comes in when we find our own unique balance of masculine and feminine (hint: if you haven’t tried intentionally spending some time totally “out” of balance, you may not know what it’s like to feel totally in). Culture seems to push people towards the extremes, cross-dressing helps undo this programming and points to another realm that is beyond dualities and into what is possible: anything.

10. You may discover your very own unique gender and maybe even that it isn’t about what you wear but how you feel. While the feeling of silk panties or leather on your skin may be wonderful, resilience and serenity are greater qualities when they are together.



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Assistant Editor: Jen Weddle/Editor: Rachel Nussbaum

Photo: elephant archives


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